Polymerizable monomers and method of polymerizing the same
AssigneeAlign Technology, Inc.
InventorsRobert Liska, Christian Gorsche, Markus Kury, Yan Chen, Chunhua Li, Srinivas Kaza
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Abstract
Provided herein are photopolymerizable monomers, optionally for use as reactive diluents in a high temperature lithography-based photopolymerization process, a method of producing polymers using said photopolymerizable monomers, the polymers thus produced, and orthodontic appliances comprising the polymers.
Claims31
A method of using a (meth)acryloyloxy-substituted benzoic acid ester of general formula (III):
- wherein,
- R1 is C3-C10 cycloalkyl or C6-C10 aryl, wherein the C3-C10 cycloalkyl and C6-C10 aryl are unsubstituted or substituted with one or more substituents selected from C1-C6 alkyl and C1-C6 alkoxy;
- R2 is H or CH3;
- the R3's are each independently C1-C6 alkyl or C1-C6 alkoxy;
- n is an integer from 0 to 4;
- and
- X and Y are each independently absent or C1-C3 alkylene, with the proviso that, when R1 is C6-C10 aryl, Y is C1-C3 alkylene;
- as a reactive diluent in a process for polymerizing a curable composition comprising at least one polymerizable species, the process comprising the steps of providing the curable composition, mixing the curable composition with the reactive diluent, and polymerizing the mixture to form a crosslinked polymer,
- wherein the curable composition comprises at least one photopolymerization initiator and is irradiated to initiate polymerization in the polymerization step, wherein the curable composition is heated to a predetermined elevated process temperature in the range of 90° C. to 120° C. before being irradiated with light having a suitable wavelength to be absorbed by the photoinitiator, thereby causing cleavage of the photoinitiator to induce polymerization of the curable composition to obtain the crosslinked polymer;
- wherein the (meth)acryloyloxy-substituted benzoic acid ester is a 2- or 3-substituted benzoic acid ester having the (meth)acryloyloxy substituted at a meta- or ortho-position of the benzoic acid ester;
- wherein the C1-C6 alkyl groups comprise linear, branched and cyclic alkyl groups;
- wherein the C1-C3 alkylene groups comprise linear, branched and cyclic alkylene groups;
- and
- wherein the process for polymerizing the curable composition is part of a 3D printing process.
An orthodontic device comprising a crosslinked polymer comprising meta- or ortho-substituted benzoic acid ester derivatives of formula (IV) as repeating units:
- wherein:
- the dotted lines each represent a bond to another carbon atom in the polymer chain;
- R1 is C3-C10 cycloalkyl or C6-C10 aryl, wherein the C3-C10 cycloalkyl and C6-C10 aryl are unsubstituted or substituted with one or more substituents selected from C1-C6 alkyl and C1-C6 alkoxy;
- R2 is H or CH3;
- Each R3 is independently C1-C6 alkyl or C1-C6 alkoxy;
- n is an integer from 0 to 4;
- X and Y are each independently absent or C1-C3 alkylene, with the proviso that, when R1 is C6-C10 aryl, Y is C1-C3 alkylene;
- the C1-C6 alkyl groups comprise linear, branched and cyclic alkyl groups, and
- the C1-C3 alkylene groups comprise linear, branched and cyclic alkylene group.
An orthodontic appliance obtained by a 3-D printing process, the orthodontic appliance comprising a polymeric material derived from a composition comprising a (meth)acryloyloxy-substituted benzoic acid ester having one of the following structures:
- wherein the polymeric material has viscoelastic behavior in the temperature range from 20° C. to 40° C.
A method of using a (meth)acryloyloxy-substituted benzoic acid ester of general formula (III):
- wherein,
- R1 is C3-C10 cycloalkyl or C6-C10 aryl, wherein the C3-C10 cycloalkyl and C6-C10 aryl are unsubstituted or substituted with one or more substituents selected from C1-C6 alkyl and C1-C6 alkoxy;
- R2 is H or CH3;
- the R3's are each independently C1-C6 alkyl or C1-C6 alkoxy;
- n is an integer from 0 to 4;
- and
- X and Y are each independently absent or C1-C3 alkylene, with the proviso that, when R1 is C6-C10 aryl, Y is C1-C3 alkylene;
- as a reactive diluent in a process for polymerizing a curable composition comprising at least one polymerizable species, the process comprising the steps of providing the curable composition, mixing the curable composition with the reactive diluent, and polymerizing the mixture to form a crosslinked polymer, wherein the step of mixing the curable composition with the reactive diluent is performed after heating at least one of:
- (a) the curable composition;
- and
- (b) the reactive diluent;
- wherein the curable composition comprises at least one photopolymerization initiator and is irradiated to initiate polymerization in the polymerization step;
- wherein the C1-C6 alkyl groups comprise linear, branched and cyclic alkyl groups;
- and
- wherein the C1-C3 alkylene groups comprise linear, branched and cyclic alkylene groups.
Dependencies are inferred from the claim text.